Reaktion #4528

Reaktionsgleichung

L-aspartic acid

dioxane water

triethylamine

tert-butyl 1,2,2,2-tetrachloroethyl carbonate

→

expected acid

Ausbeute 60.0%

tert-butyloxycarbonyl-L-aspartic acid

Ausbeute 60.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(approximately 10 min)
2. 2
   workup.STIRRINGthe mixture is stirred for 6 hours at 20° C
3. 3
   Extraktionthe mixture is extracted with 2×20 ml of ethyl acetate
4. 4
   Extraktionextracted with 3×30 ml of ethyl acetate
5. 5
   WaschenThe extract is washed with saturated NaCl solution
6. 6
   Trocknendried over MgSO4
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe product obtained
9. 9
   Sonstigeis crystallised in ethyl acetate

Vorschrift

To a solution of 1.33 g (10 mmol) of L-aspartic acid in a dioxane/water (1:1) mixture (30 ml), 4.2 ml (30 mmol) of triethylamine are added, and the mixture is stirred until solution is complete (approximately 10 min). 2.85 g (10 mmol) of tert-butyl 1,2,2,2-tetrachloroethyl carbonate are then added and the mixture is stirred for 6 hours at 20° C. 50 ml of water are then added and the mixture is extracted with 2×20 ml of ethyl acetate. The aqueous phase is acidified (pH 2-3) with NHCl, and then extracted with 3×30 ml of ethyl acetate. The extract is washed with saturated NaCl solution, dried over MgSO4 and evaporated. The product obtained is crystallised in ethyl acetate and petroleum ether. 1.4 g (60% yield) of the expected acid is obtained. ##STR60##

Quelle